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Synthesis, Ionisation Potentials and Electron Affinities of Hexaazatrinaphthylene Derivatives

“…[11,12] The diamines were either commercially www.chemeurj.org available (for 1 and 7) or were synthesised using literature procedures (for 8 and 9). [13][14][15][16] Compound 3 a was obtained from 7 according to the literature procedure. [6] These compounds were very poorly soluble in organic solvents and were, therefore, purified by gradient sublimation under high vacuum.…”

“…The product was purified by flash chromatography on silica gel eluting with hexane/ethyl acetate (10:2) to give 1.00 g (63 %) of purified product. [13,14] (3.85 g, 26.71 mmol) was added to deoxygenated acetic acid (250 mL). The mixture was refluxed for 16 h. After the mixture was cooled to room temperature, the solid was collected by filtration and was washed with acetic acid to give a yellow solid (2.88 g, 58 % crude yield).…”

Fluorinated benzazoles and benzazines

“…2-Mercapto-5,6-difluorobenzimidazole 1 was shown to react with aromatic α-haloketones to give 2-phenacylthio-5,6-difluorobenzimidazoles 2. The latter were transformed by acylation and cyclodehydration in an acetic anhydride-pyridine system into benzo [4,5] [13]. Biological tests revealed that compound 4 (Ar = C 6 H 5 ) displayed a considerable activity toward the meastle virus [14].…”

“…By reacting with β-ketoesters, 1H-5,6-difluorobenzimidazol-2-acetonitrile 5 was transformed into pyrido[1,2-a]-benzimidazoles 6 and 7 (Scheme 3), which proved to be active against pathogenic orthopox viruses [15,16]. SCHEME 2 SCHEME 3 SCHEME 4…”

“…Features of tautomerism in the series of furoxanes 8 (R = F, morpholino) have been studied by 1 H, 13 C, and 19 F NMR methods. The factors affecting tautomeric equilibria as well as thermodynamic characteristics of both isomers have been determined (Scheme 4) [17,18].…”